ArticleSynlett : accounts and rapid communications in synthetic organic chemistry2019
Biocatalytic synthesis of α-amino ketones.
Article in Synlett : accounts and rapid communications in synthetic organic chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Versatile Chemo-Biocatalytic Cascade Driven by a Thermophilic and Irreversible C-C Bond-Forming α-Oxoamine Synthase.ACS sustainable chemistry & engineering · 2023Article
- Structural Basis for Control of Methylation Extent in Polyketide Synthase Metal-DependentACS chemical biology · 2022Article
- Direct Addition of Grignard Reagents to Aliphatic Carboxylic Acids Enabled by Bulky turbo-Organomagnesium Anilides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Broadening the scope of biocatalytic C-C bond formation.Nature reviews. Chemistry · 2020Article
- Identification of promoter elements in the Dolichospermum circinale AWQC131C saxitoxin gene cluster and the experimental analysis of their use for heterologous expression.BMC microbiology · 2020Article
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Authors and funding
2 authors.
Funding
Abstract
Stereospecific generation of α-amino ketones from common α-amino acids is difficult to achieve, often employing superstoichiometric alkylating reagents and requiring multiple protecting group manipulations. In contrast, the α-oxoamine synthase protein family performs this transformation stereospecifically in a single step without the need for protecting groups. Herein, we detail the characterization of the 8-amino-7-oxononanoate synthase (AONS) domain of the four-domain polyketide-like synthase SxtA, which natively mediates the formation of the ethyl ketone derivative of arginine. The function of each of the four domains is elucidated, leading to a revised proposal for the initiation of saxitoxin biosynthesis, a potent neurotoxin. We also demonstrate the synthetic potential of SxtA AONS, which is applied to the synthesis of a panel of novel α-amino ketones.
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